Free-online migration: unable to send emails

[#1]

I'm now at least able to receive emails via Outlook again: the problem there was with a character I was using in the password, which I've changed. Still not able to send emails, though, which does now look as if it's just the Port 25 issue.

Error Code -3253

[#2 · Accepted solution]

Sorted! Found an outgoing port that works!

[#3]

So do you want to share the settings that me help others?

[#4]

@Townman Apologies for not being clear.

It is possible I should've started a new thread.  On second reading I guess this is a slightly different scenario to the OP where they were using a third party app to connect.

For context, my parents are 3 hours away from me and I do not have remote access or screen sharing capabilities with them.  I am trying to gather what info I can from them over the phone and photos of what's on their monitor.

While I understand where you are coming from on the difference between not being able to send emails and gmail not accepting, the end result to them as lay people in their 80s is that they are unable to send to emails me at my gmail address, and their test emails to their own gmail accounts also fail.

Let's start over....

They have never received the "Welcome to Greenby" email so any useful information that it may have contained is out of our reach.

Greenby WEBMAIL is being used.  i.e. they are not using POP3 or SMTP to connect with Greenby servers using a third party application.  

From what they have described to me, they log into the greenby.com portal (not webmail.greenby.com)

From there they navigate to webmail.  (I think I set this up years ago to accept their single email address as an alias and "postmaster".  I think I disabled catch-all.)

In webmail they compose an email to [somebody]@gmail.com and send.

Within a few seconds they receive an "undelivered message" email from the gmail servers refusing the email because it is unauthenticated.  I have attached photos of the (redacted) message that comes back.

Since the original post above I have tested a non-gmail address with them.  I can confirm that they can successfully send to non-gmail addresses using the Greenby webmail portal.

If the mods feel this post is better moved to its own thread, please do so.

[#5]

@FridayFeeling  No doubt @Townman  (or @MisterW ?) will correct me if I am wrong, but if your parents authenticate their email connection, this problem should be resolved.

[#6]

@jab1 I think there's a misunderstanding of what google means by 'authentication' 

Its not authentication of the smtp connection from the email client when submitting the email, its whether SPF and/or DKIM are enabled on the domain i.e is the server 'authorised' to send mail for that domain.

There's some uncertainty as to whether SPF/DKIM are enabled on migrated accounts , its been raised to the business 

[#7]

Ah, OK @MisterW . I admit to not totally understanding the nuances of the migration, so thanks for the clarification.

@FridayFeeling Ignore my previous post.

[#8]

TBH it's not helped by googles incorrect use of 'authenticated' rather than 'authorised'.

[#9]

@Silverwhistle Please can you share the Port for us all who are unable to send emails. My sis-in-law has the same issue, She is on an iPhone and we have tied alternative ports which are not accepted

[#10]

@lyndonp 

As per post #2 - it should be 587 with STARTTLS.

[#11]

Unfortunately that doesn’t work. We had already tried that with SSL on and off. Also tried 465 and some others restarting the iphone and clearing out the Outbox after each failure.

Judging by people with issues on here and on the EE forum this Greenby migration has not gone well. Don’t seem to be getting anywhere with their tech support either.

Can’t Plusnet technical get involved with Greenby to sort this mess out. After all it is PN who initiated this migration and should have some duty of care if only for goodwill to their own customers.

I don’t know what the rollout is as fortunately I moved my emails from PN some time back but my concern is I also have a 94 year old father in law with a plus.com email address who may suffer the same issues who won’t know what to do if the migration is not seamless.

[#12]

Without a shadow of doubt, for SMTP the correct port is 587 with STARTTLS.  That said some email clients are defective in that they do not support STARTTLS.  In which case obsolete standards need to be considered - that is as a very last resort use port 465 with SSL.

If that does not work, then that is not the problem.  Its your logon on credentials.

Use the email server connection diagnostic test - see the link below.

Some indication of the error codes being returned would be helpful.

If email clients are set up properly in the first place, migration is seamless.  In various characteristics Plusnet's servers were not strict with authentication details, allowing tokens other than the email address as the userID to be used for authentication.

[#13]

She is using the standard iPhone IoS Mail app so fairly common for many users. IoS version current

All the information from Greenby is to use Port 25 and SSL set to None so there is certainly an issue with Greenby putting this information out if it is incorrect. See screenshot from Greenby.

If it is 587 like you say then it does not work and STARTTLS cannot be selected only SSL on/off in the SMTP settings. Neither work nor does using 465 (and why don't Greenby state this in their tech support if 25 is incorrect?)

Never been an issue with PN.

Logon credentials are correct as it validates the SMTP settings with the username/password. On sending an email it comes out with "Cannot send mail The sender address is invalid".No other error messages. Using the same password for incoming which works so unless Greenby have an issue with SMTP username/password it cannot be incorrect.

The diagnosing doesn't add anyting different to which we have checked.

Greenby have an issue which they need to respond and PN should push them on it. Been going on a week. Total farce and poor support.

[#14]

---

@lyndonp wrote:

On sending an email it comes out with "Cannot send mail The sender address is invalid".

---

That has probably zero to do with port settings, authentication etc ... I'm guessing that you get that no matter what port you use?  In iOS the only thing you need to worry about is does it return an error when you click "Done" on the settings ... or do you get blue ticks all round?

Regardless of what Greenby's advice is, using port 25 is just very bad practice and utterly not compliant with the RFC standard for email message SUBMISSION by an email CLIENT.  Port 25 is reserved and designated by RFC standards for MTA to MTA message RELAY only.  Port 465 is obsolete.

To get the error message above, you are actually connected to the SMTP server.  Is the email address configured in the iOS account details the same as that for the mailbox - that is, not an alias or alternative identity? For example is the mailbox is account@account.free-online.co.uk and the sending address has been configured as postmaster@account.free-online.co.uk (which is quite legitimate) then there's some chance that issues will be encountered - for example - 550 5.7.1 Unknown sender

Is the userID being used the email address or the accountID?

Can you login OK and send using webmail?

This is also a possibility...

Sender Domain Rejected (black listed by local policy)

This issue can report as server error 550. It typically arises where a user's email address has been abused for the purposes of sending spam emails. It has nothing to do with server settings etc.

This requires intervention by staff to determine the cause of the problem and to issue advice to check your system for viruses and malware. Only after your system(s) have been affirmed to be clean can the black listing be lifted. As a precaution, you should change the password on the affected email address.

Add your details to this thread - Cannot Send Emails and send a PM to @Leanne_T

[#15]

---

@Townman wrote:

... In which case obsolete standards need to be considered - that is as a very last resort use port 465 with SSL.

Not quite the "very last resort".

My last resort would be port 2525 with or without STARTTLS (using TLS v1.2 or v1.3)

This port 2525 was originally used to bypass networks which blocked SMTP using port 25,

HOWEVER, while port 25 is used as an SMTP 'relay',  this alternative port 2525 is a SMTP 'submission'

@Townman  it would be interesting to know using your email diagnostics, whether port 2525 responds on Greenby ?